Compound, resin, polycarbonate resin, and optical molded article

ABSTRACT

Provided is a compound represented by General Formula (1) 
     
       
         
         
             
             
         
       
     
     in General Formula (1), Ar 1  and Ar 2  independently represent a group selected from the following Formulae,

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. Application No. 17/779,161,filed on May 24, 2022, which is a U.S. national stage application ofPCT/JP2021/027779, filed on Jul. 27, 2021, which claims priority toJapanese Patent Application No. 2020-127221, filed on Jul. 28, 2020, theentire contents of all of which are hereby incorporated by reference.

TECHNICAL FIELD

The present invention relates to a compound, a resin obtained from thecompound or a polycarbonate resin, and an optical molded articlecontaining the resin or the polycarbonate resin.

BACKGROUND ART

Optical glass or an optical resin is used as a material for an opticallens used in an optical system of various kinds of cameras such as acamera, a film-integrated camera, and a video camera. The optical glassis excellent in heat resistance, transparency, dimensional stability,chemical resistance, and the like, and there are various kinds ofmaterials having various refractive indices and Abbe numbers. However,there are problems that the material cost is high, the moldingprocessability is poor, and the productivity is low.

On the other hand, an optical lens formed of an optical resin has anadvantage that mass production can be achieved by injection molding. Forexample, a polycarbonate resin or the like is used in camera lenses.However, in recent years, there has been a demand for the development ofresins having a high refractive index due to lightness, thinness,shortness, and miniaturization of products. In general, since in a casewhere the refractive index of an optical material is high, lens elementshaving the same refractive index can be realized with a surface having asmaller curvature, the aberration amount generated on this surface canbe reduced. As a result, it is possible to reduce the number of lenses,reduce the eccentricity sensitivity of a lens, and reduce the thicknessand weight of a lens.

Examples of techniques related to the optical resin include thosedescribed in Patent Documents 1 and 2.

In Patent Document 1 (Japanese Unexamined Patent Publication No.2005-241962), an optical lens that is formed of a polycarbonate resinhaving a fluorene structure is described.

In Patent Document 2 (Japanese Unexamined Patent Publication No.2005-187661), a method for easily improving a refractive index byblending (mixing and adding) a sulfur-containing compound with afluorene-containing polyester is described.

RELATED DOCUMENT Patent Documents

-   [Patent Document 1] Japanese Unexamined Patent Publication No.    2005-241962-   [Patent Document 2] Japanese Unexamined Patent Publication No.    2005-187661

SUMMARY OF THE INVENTION Technical Problem

However, the polycarbonate resin as described in Patent Document 1 has alow refractive index and is not a sufficiently satisfactory resin.

In addition, as described in Patent Document 2, in a case where thesulfur-containing compound is blended with the fluorene-containingpolyester, the refractive index is improved. However, in a case wherethe heat stability is lowered due to the addition of a low molecularweight component, and the compatibility of the two components to beblended is poor, the transparency may decrease.

The present invention has been made in view of the above circumstances,and an object of the present invention is to provide a resin and apolycarbonate resin capable of realizing an optical molded articlehaving a high refractive index and excellent transparency.

Solution to Problem

The present inventors have diligently studied to provide a polycarbonateresin capable of realizing an optical molded article having a highrefractive index and excellent transparency. As a result, the presentinventors have found that an optical molded article having a highrefractive index and excellent transparency can be realized by a resinobtained by polymerization of a compound represented by the followingFormula (1), and have reached the present invention.

According to the present invention, a compound represented by thefollowing General Formula (1), a resin obtained from the compound, apolycarbonate resin derived from the compound, and an optical moldedarticle are provided.

[1] A compound represented by General Formula (1),

-   in which in General Formula (1), Ar₁ and Ar₂ independently represent    a group selected from the following Formulae,

-   

-   

-   

-   

-   

-   

-   

-   

-   

-   

-   

-   

-   

-   

-   where, R₁ to R₆ each represent a hydrogen atom, a hydrocarbon group,    or a heteroatom-containing hydrocarbon group,

-   A₁ to A₅ and B₁ to B₅ each represent a hydrogen atom, a hydrocarbon    group, or a heteroatom-containing hydrocarbon group,

-   at least one of A₁ to A₅ is a —Y₁—Ar₃ group,

-   at least one of B₁ to B₅ is a —Y₂—Ar₄ group,

-   Y₁ and Y₂ each represent a single bond or a linking group,

-   Ar₃ and Ar₄ each represent an aromatic group,

-   X₁ to X₄ each are —O—, —S—, —NR′—, or —C(Me)₂—,

-   Z₁ to Z₄ each represent a hydrocarbon atom, a hydrocarbon group, or    a heteroatom-containing hydrocarbon group,

-   R′ represents a hydrogen atom, a hydrocarbon group, or a    heteroatom-containing hydrocarbon group, and

-   o and p each represent an integer of 1 to 4.

The compound according to [1], in which in General Formula (1), o and peach are 2.

The compound according to [1] or [2], in which in General Formula (1),Ar₁ and Ar₂ independently represent a group selected from the followingformulae,

-   R₁ to R₆ each represent a hydrogen atom, a hydrocarbon group, or a    heteroatom-containing hydrocarbon group, and-   o and p each represent an integer of 1 to 4.

A resin obtained by polymerization of the compound represented byGeneral Formula (1) according to any one of [1] to [3].

A polycarbonate resin derived from the compound represented by GeneralFormula (1) according to any one of [1] to [3].

An optical molded article containing the resin according to [4] or [5].

The optical molded article according to [6], in which the optical moldedarticle is an optical lens.

The optical molded article according to [6], in which the optical moldedarticle is an optical film.

Advantageous Effects of Invention

According to the present invention, it is possible to provide the resinand the polycarbonate resin capable of realizing the optical moldedarticle having the high refractive index and excellent transparency.

DESCRIPTION OF EMBODIMENTS

Hereinafter, embodiments of the present invention will be described.Unless otherwise specified, the term “to” between the numerical valuesin the text indicates a range of equal to or more than a numerical valueand equal to or less than a numerical value.

Compound

A compound according to the present embodiment will be described. Thecompound according to the present embodiment is a compound representedby General Formula (1).

In General Formula (1), Ar₁ and Ar₂ independently represent a groupselected from the following formulae,

-   where, R₁ to R₆ each represent a hydrogen atom, a hydrocarbon group,    or a heteroatom-containing hydrocarbon group,-   A₁ to A₅ and B₁ to B₅ each represent a hydrogen atom, a hydrocarbon    group, or a heteroatom-containing hydrocarbon group, at least one of    A₁ to A₅ is a —Y₁—Ar₃ group,-   at least one of B₁ to B₅ is a —Y₂—Ar₄ group,-   Y₁ and Y₂ each represent a single bond or a linking group, Ar₃ and    Ar₄ each represent an aromatic group, X₁ to X₄ each are —O—, —S—,    —NR′—, or —C(Me)₂—,-   Z₁ to Z₄ each represent a hydrogen atom, a hydrocarbon group, or a    heteroatom-containing hydrocarbon group,-   R′ represents a hydrogen atom, a hydrocarbon group, or a    heteroatom-containing hydrocarbon group, and-   o and p each represent an integer of 1 to 4.

In General Formula (1), R₁ to R₆ each are preferably independentlyselected from a hydrogen atom and an alkyl group having 1 to 3 carbonatoms or an aryl group having 6 to 20 carbon atoms, R₁ to R₆ each aremore preferably independently selected from a hydrogen atom, a methylgroup, a phenyl group, a biphenyl group, a naphthyl group, and R₁ to R₆each are even more preferably a hydrogen atom.

In General Formula (1), o and p each are an integer of 1 to 4,preferably an integer of 1 or 2, and more preferably an integer of 2. Bysetting o and p to the above range, a polycarbonate resin obtained fromthe compound of General Formula (1) has excellent heat resistance.

In one embodiment, Ar₁ and Ar₂ in General Formula (1) independentlyrepresent a group selected from the following formulae,

-   R₁ to R₆ each represent a hydrogen atom, a hydrocarbon group, or a    heteroatom-containing hydrocarbon group, and-   o and p each represent an integer of 1 to 4.

Examples of preferred aspects of Ar₁ and Ar₂ in General Formula (1) eachinclude the following formulae.

Examples of the compound represented by General Formula (1) include9,9-bis(1′-hydroxymethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-dinaphthalen-1″-yl-9H-fluorene,9,9-bis(1′-hydroxymethyl)-3,6-dinaphthalen-2″-yl-9H-fluorene,9,9-bis(1′-hydroxymethyl)-3,6-dinaphthalen-1″-yl-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-di-p-biphenyl-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-di-m-biphenyl-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-bis(3″,5″-diphenylphenyl)-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-bis[dibenzo[b,d]thiophen-4″-yl]-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-bis(4″-phenoxyphenyl)-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-bis(4″-phenylnaphthalen-1″-yl)-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-bis[4-(naphthalen-2-yl)phenyl]-9H-fluorene,9,9-bis(1′-hydroxymethyl)-2,7-bis[3-(naphthalen-2-yl)phenyl]-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-1″-yl-9H-fluorene,9,9-bis(2′-hydroxyethyl)-3,6-dinaphthalen-2″-yl-9H-fluorene,9,9-bis(2′-hydroxyethyl)-3,6-dinaphthalen-1″-yl-9H-naphthalene,9,9-bis(2′-hydroxyethyl)-2,7-di-p-biphenyl-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-di-m-biphenyl-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-di-o-biphenyl-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis(3″,5″-diphenylphenyl)-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]]furan-4″-yl]-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]thiophen-4″-yl]-9H-fluorene,9,9-bis (2′-hydroxyethyl)-2,7-bis (4″-phenoxyphenyl)-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis(3″,5″-diphenoxyphenyl)-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis(4″-phenylnaphthalen-1″-yl)-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis[4-(naphthalen-2-yl)phenyl]-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis[3-(naphthalen-2-yl)phenyl]-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis[3-(naphthalen-1-yl)phenyl]-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis[4-(naphthalen-1-yl)phenyl]-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-diphenanthryl-9″-yl-9H-fluorene,9,9-bis(2′-hydroxyethyl)-2,7-bis[9″,9″-dimethyl-9″-fluoren-2″-yl]-9H-fluorene,9,9-bis(3′-hydroxypropyl)-2,7-dinaphthalen-2″-yl-9H-fluorene,9,9-bis(3′-hydroxypropyl)-2,7-dinaphthalen-1″-yl-9H-fluorene,9,9-bis(3′-hydroxypropyl)-3,6-dinaphthalen-2″-yl-9H-fluorene,9,9-bis(3′-hydroxypropyl)-3,6-dinaphthalen-1″-yl-9H-naphthalene,9,9-bis(4′-hydroxybutyl)-2,7-dinaphthalen-2″-yl-9H-fluorene,9,9-bis(4′-hydroxybutyl)-2,7-dinaphthalen-1″-yl-9H-fluorene,9,9-bis(4′-hydroxybutyl)-3,6-dinaphthalen-2″-yl-9H-fluorene,9,9-bis(4′-hydroxybutyl)-3,6-dinaphthalen-1″-yl-9H-naphthalene,9,9-bis(4′-hydroxybutyl)-3,6-bis[4-(naphthalen-2-yl)phenyl]-9H-fluorene,and the like.

Among these, preferred examples thereof can include9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene, and9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-1″-yl-9H-fluorene. Such acompound may be used alone or two or more compounds may be used incombination.

Method for Producing Compound Represented by General Formula (1)

The compound represented by General Formula (1) according to the presentembodiment can be synthesized by the following steps (i) and (ii).

Step (i): Dihalogeno-9H-fluorene such as 2,7-dibromo-9H-fluorene or3,6-dibromo-9H-fluorene is treated with a base (for example, sodiumhydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,sodium hydride, potassium hydride, methoxy sodium, ethoxy sodium,t-butoxy sodium, t-butoxy potassium, and n-butyllithium) in a solvent(for example, tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide,N,N-dimethylacetamide, dimethylsulfoxide, and sulfolane) to extract 9thhydrogen of dihalogeno-9H-fluorene, and thereafter, reacts withhydroxyalkyl having a leaving group (here, examples of a leaving groupcan include halogen such as chlorine, bromine, iodine, ap-toluenesulfonyloxy group, a methylsulfonyloxy group, atrifluoromethylsulfonyloxy group, and the like) to produce9,9-bis(hydroxyalkyl)-dihalogeno-9H-fluorene such as9,9-bis(hydroxyalkyl)-2,7-dibromo-9H-fluorene or9,9-bis(hydroxyalkyl)-3,6-dibromo-9H-fluorene.

Step (ii): 9,9-bis(hydroxyalkyl)-dihalogeno-9H-fluorene such as9,9-bis(hydroxyalkyl)-2,7-dibromo-9H-fluorene or9,9-bis(hydroxyalkyl)-3,6-dibromo-9H-fluorene, which is obtained in Step(i), reacts with naphthyl boric acid in a solvent (for example, tolueneand water, tetrahydrofuran and water, and dimethyl sulfoxide and water)in the presence of a base (for example, sodium carbonate, potassiumcarbonate, sodium acetate, potassium acetate, sodium phosphate, andpotassium phosphate) and a palladium-based catalyst such as and tetrakispalladium (triphenylphosphine) to produce the compound represented byGeneral Formula (1) of purpose under a condition of so-calledSuzuki-Miyaura Coupling.

Here, the reaction of step (i) can be carried out at any temperaturebetween -78° C. and the boiling point of the solvent. In addition, asreaction conditions, general alkylation reaction conditions can beapplied. As desired, a hydroxy group of hydroxyalkyl having a leavinggroup is protected with any protecting group (for example, an estergroup such as an acetyl group), an ether group such as atetrahydropyranyl group, a carbonic acid ester group such as at-butoxycarbonyl group, and then may be deprotected at the end.

The reaction of step (ii) can be carried out at any temperature betweenroom temperature and the boiling point of the solvent. As reactionconditions, the reaction conditions generally used in the so-calledSuzuki-Miyaura coupling can be applied.

[Resin]

One aspect of the present invention is a resin obtained bypolymerization of a compound represented by General Formula (1). Here,examples of the resin obtained by polymerization of the compoundrepresented by General Formula (1) include a polyester resin, apolyurethane resin, a polycarbonate resin, and a polyether resin.

The polyester resin can be obtained by reacting the compound representedby General Formula (1) with an aromatic dicarboxylic acid (for example,terephthalic acid, isophthalic acid, or 2,6-naphthalenedicarboxylicacid), or an aliphatic dicarboxylic acid (for example, oxalic acid,malonic acid, or succinic acid).

The polyurethane resin can be obtained by reacting the compoundrepresented by General Formula (1) with an aromatic diisocyanate (forexample, toluene diisocyanate or xylylene diisocyanate) or an aliphaticdiisocyanate (for example, pentamethylene diisocyanate, hexamethylenediisocyanate, or cyclohexanedimethylene diisocyanate).

As will be described later, the polycarbonate resin can be obtained byreacting the compound represented by General Formula (1) with acarbonate precursor such as a carbonic acid diester.

The polyether resin can be obtained by reacting the compound representedby General Formula (1) with an aliphatic dihalogen compound (forexample, dibromoethane or dibromopropane) in presence of a base.

In these resins, a reactant other than the compound represented byGeneral Formula (1) of the present application may be used alone or aplurality of reactants may be used in combination. In addition, it isalso possible to polymerize a resin by using a dihydroxy compound otherthan the compound represented by General Formula (1) of the presentapplication, in combination.

In a case where the dihydroxy compound other than the compoundrepresented by General Formula (1) of the present application is used incombination, a ratio of the compound represented by General Formula (1)to the total amount of the compound represented by General Formula (1)of the present application and the dihydroxy compound other than thecompound represented by General Formula (1) is preferably equal to ormore than 5 mol% and equal to or less than 99 mol%, more preferablyequal to or more than 10 mol% and equal to or less than 99 mol%, andeven more preferably equal to or more than 15 mol% and equal to or lessthan 99 mol%.

Here, examples of the dihydroxy compound other than the compoundrepresented by General Formula (1) include bis(4-hydroxyaryl)alkanessuch as9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-ethylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-n-propylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-n-butylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-sec-butylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-tert-butylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-cyclohexylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-2-phenylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-(3-methylphenyl)phenyl]fluorene,bis[4-(2′-hydroxyethoxy)phenyl]sulfide,bis[4-(2′-hydroxyethoxy)-3-methylphenyl]sulfide,bis[4-(2′-hydroxyethoxy)phenyl]sulfone,bis[4-(2′-hydroxyethoxy)-3-methylphenyl]sulfone,bis[4-(2′-hydroxyethoxy)phenyl]sulfoxide, bis(4-hydroxyphenyl)methane,2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)ethane,1,1-bis(4-hydroxyphenyl)phenylethane,2,2-bis(4-hydroxy-3-methylphenyl)propane,2,2-bis(4-hydroxyphenyl)heptane,2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane,2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, and4,4-dihydroxyphenyl-1,1-m-diisopropylbenzene;bis(hydroxyaryl)cycloalkanes such as1,1-bis(4-hydroxyphenyl)cyclopentane,1,1-bis(4-hydroxyphenyl)cyclohexane,1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, and2,2,2,2-tetrahydro-3,3,3,3-tetramethyl-1,1-spirobis[1H inden]-6,6-diol;dihydroxyaryl ethers such as bis(4-hydroxyphenyl)ether, andbis(4-hydroxy-3,5-dichlorophenyl)ether;9,9-bis(4-hydroxyphenyl)fluorene,9,9-bis(4-hydroxy-3-methylphenyl)fluorene,9,9-bis(4-hydroxy-3-tert-butylphenyl)fluorene,9,9-bis(4-hydroxy-3-isopropylphenyl)fluorene,9,9-bis(4-hydroxy-3-cyclohexylphenyl)fluorene, and9,9-bis(4-hydroxy-3-phenylphenyl)fluorene; ethylene glycol,1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol,1,4-cyclohexanedimethanol, 2,2-dimethyl-1,3-propanediol,1,10-decanediol, diethylene glycol, tetraethylene glycol, norbornanedimethanol, decahydronaphthalenedimethanol,tricyclo[5.2.1.0^(2,6)]decandimethanol, pentacyclopentadecanedimethanol,cyclopentane-1,3-dimethanol, spiroglycol, and the like.

[Polycarbonate Resin]

The polycarbonate resin according to the present embodiment is producedby using the compound represented by General Formula (1) according tothe present embodiment. The polycarbonate resin according to the presentembodiment has a structural unit represented by Formula (1p) and derivedfrom the compound represented by General Formula (1). Such apolycarbonate resin can realize an optical molded article having a highrefractive index and excellent transparency. As a result, thepolycarbonate resin can be suitably used as a material for an opticallens.

In Formula (1p), Ar₁ and Ar₂, R₁ and R₂, and o and p each are synonymouswith those in Formula (1). The same applies to the preferred aspects.

A preferred weight average molecular weight in terms of polystyrene (Mw)of the polycarbonate resin according to the present embodiment ispreferably equal to or greater than 1.5 × 10³ and equal to or smallerthan 2.0 × 10⁵, and more preferably equal to or greater than 2.0 × 10³and equal to or smaller than 1.2 × 10⁵.

In a case where Mw is equal to or greater than the above lower limitvalue, it is preferable that the obtained molded article can besuppressed from being fragile. In a case where Mw is equal to or smallerthan the above upper limit value, the melt viscosity becomes moreappropriate, so that the resin can be easily taken out after production,fluidity further becomes better, and injection molding becomes easier ina molten state, which are preferable.

A refractive index (n633) of the polycarbonate resin according to thepresent embodiment at 23° C. and a wavelength of 633 nm is preferablyequal to or greater than 1.70 and equal to or smaller than 1.85, morepreferably equal to or greater than 1.70 and equal to or smaller than1.82, even more preferably equal to or greater than 1.71 and equal to orsmaller than 1.81, and particularly preferably equal to or greater than1.72 and equal to or smaller than 1.81.

The polycarbonate resin according to the present embodiment can beblended with another resin and used for producing a molded article.Examples of other resins include polyamide, polyacetal, polycarbonate,modified polyphenylene ether, polyethylene terephthalate, polybutyleneterephthalate, and the like.

Furthermore, an antioxidant, a mold release agent, an ultravioletabsorber, a fluidity modifier, a crystal nucleating agent, astrengthening agent, a dye, an antistatic agent, an antibacterial agent,and the like can be added to the polycarbonate resin according to thepresent embodiment.

Examples of a molding method include compression molding, casting, rollprocessing, extrusion molding, stretching, and the like, in addition toinjection molding, but the molding method is not limited thereto.

In a case where the polycarbonate resin according to the presentembodiment is used for injection molding, the glass transitiontemperature (Tg) is preferably equal to or higher than 80° C. and equalto or lower than 190° C., more preferably equal to or higher than 85° C.and equal to or lower than 180° C., and even more preferably equal to orhigher than 90° C. and equal to or lower than 170° C. In a case where Tgis equal to or higher than the above lower limit value, a range oftemperature in use is wider, which is preferable. In a case where Tg isequal to or lower than the above upper limit value, the meltingtemperature of the resin decreases, and decomposition and coloring ofthe resin are less likely to occur, which is preferable. In addition, ina case where Tg is equal to or lower than the above upper limit value,the difference between the mold temperature and the resin glasstransition temperature can be reduced even with a general-purpose moldtemperature controller. Therefore, it is easy to use and preferable inapplications in which strict surface accuracy is required for a product.

The optical molded article obtained by using the polycarbonate resinaccording to the present embodiment preferably has a total transmittanceof equal to or greater than 82%, more preferably has a totaltransmittance of equal to or greater than 85%, in which each totaltransmittance is measured in accordance with JIS K-7361-1 (1997), and isby no means inferior to a bisphenol A-type polycarbonate resin and thelike.

Method for Producing Polycarbonate Resin

The polycarbonate resin according to the embodiment can be produced byusing the compound represented by General Formula (1) as a raw material.Specifically, the compound represented by General Formula (1) reactswith a carbonate precursor such as a carbonic acid diester by a meltpolycondensation method, in presence of a basic compound catalyst, atransesterification catalyst, or a mixed catalyst constituted of both,or in absence of a catalyst, to produce the polycarbonate resin.

Examples of the carbonic acid diester used to produce the polycarbonateresin according to the present embodiment include diphenyl carbonate,di-p-tolyl carbonate, di-m-tolyl carbonate, di-o-tolyl carbonate,bis(p-chlorophenyl)carbonate, bis(m-chlorophenyl)carbonate,bis(o-chlorophenyl)carbonate, m-cresyl carbonate, dimethyl carbonate,diethyl carbonate, di-n-butyl carbonate, dicyclohexyl carbonate, and thelike. Among these, diphenyl carbonate is preferred. Diphenyl carbonateis preferably used in a ratio of 0.97 to 1.20 mol and more preferablyused in a ratio of 0.98 to 1.10 mol, with respect to 1 mol of thecompound represented by General Formula (1).

Examples of the basic compound catalyst used in the production of thepolycarbonate resin according to the present embodiment include alkalimetal compounds, alkaline earth metal compounds, nitrogen-containingcompounds, and the like. As such compounds, organic acid salts,inorganic salts, oxides, hydroxides, hydrides or alkoxides, orquaternary ammonium hydroxides and salts thereof, amines, or the like ofalkali metals, alkaline earth metal compounds, or the like arepreferably used, and these compounds can be used alone or incombination.

Examples of the alkali metal compounds include organic acid salts,inorganic salts, oxides, hydroxides, hydrides, alkoxides, and the likeof alkali metals. Specific examples thereof for use include sodiumhydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide,sodium hydrogencarbonate, sodium carbonate, potassium hydrogencarbonate,potassium carbonate, cesium carbonate, lithium carbonate, sodiumacetate, potassium acetate, cesium acetate, lithium acetate, sodiumstearate, potassium stearate, cesium stearate, lithium stearate, sodiumborohydride, sodium borophenylate, sodium benzoate, potassium benzoate,cesium benzoate, lithium benzoate, disodium hydrogenphosphate,dipotassium hydrogenphosphate, dilithium hydrogenphosphate, disodiumphenylphosphate, a disodium salt, a dipotassium salt, a dicesium salt,or a dilithium salt of bisphenol A, a sodium salt, a potassium salt, acesium salt, or a lithium salt of phenol, and the like.

Examples of the alkaline earth metal compounds include organic acidsalts, inorganic salts, oxides, hydroxides, hydrides, alkoxides, or thelike of alkaline earth metal compounds. Specific examples thereof foruse include magnesium hydroxide, calcium hydroxide, strontium hydroxide,barium hydroxide, magnesium hydrogencarbonate, calciumhydrogencarbonate, strontium hydrogencarbonate, bariumhydrogencarbonate, magnesium carbonate, calcium carbonate, strontiumcarbonate, barium carbonate, magnesium acetate, calcium acetate,strontium acetate, barium acetate, magnesium stearate, calcium stearate,calcium benzoate, magnesium phenylphosphate, and the like.

Examples of the nitrogen-containing compounds include quaternaryammonium hydroxides and salts thereof, amines, and the like. Specificexamples thereof for use include quaternary ammonium hydroxides havingan alkyl group such as tetramethylammonium hydroxide, tetraethylammoniumhydroxide, tetra n-propylammonium hydroxide, tetra n-butylammoniumhydroxide, trimethylbenzylammonium hydroxide, or an aryl group; tertiaryamines such as triethylamine, dimethylbenzylamine, triphenylamine;secondary amines such as diethylamine and dibutylamine; primary aminessuch as n-propylamine and n-butylamine; imidazoles such as2-methylimidazole, 2-phenylimidazole, and benzoimidazole; or bases suchas ammonia, tetramethylammonium borohydride, tetra n-butylammoniumborohydride, tetra n-butylammonium tetraphenylborate,tetraphenylammonium tetraphenylborate, or basic salts, and the like.

As the transesterification catalyst, salts such as zinc, tin, zirconium,lead, and the like are preferably used, and these salts can be usedalone or in combination. Specific examples of the transesterificationcatalyst for use include zinc acetate, zinc benzoate, zinc2-ethylhexanoate, tin chloride (II), tin chloride (IV), tin acetate(II), tin acetate (IV), dibutyltin dilaurate, dibutyltin oxide,dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate,zirconium tetrabutoxide, lead acetate (II), lead acetate (IV), and thelike.

Each of these catalysts is used at a ratio of 10⁻⁹ to 10⁻³ mol,preferably 10⁻⁷ to 10⁻⁴ mol, with respect to a total of 1 mol of thecompound represented by General Formula (1).

The melt polycondensation method is a method of performing meltpolycondensation using the above described raw material and catalystunder heating and normal pressure or reduced pressure while removingby-products through a transesterification reaction.

In the melt polycondensation method according to the present embodiment,the reaction is desirably carried out in a state in which the compoundrepresented by General Formula (1) and the carbonic acid diester aremelted in a reaction vessel, and the reaction is then carried out in astate where by-product monohydroxy compounds are kept in the reactionvessel.

In order to keep the by-product monohydroxy compounds, a reactingapparatus can be closed, or can be vacuumed or pressurized for pressurecontrol purposes The reaction time required for this step is preferablyequal to or more than 20 minutes and equal to or less than 240 minutes,more preferably equal to or more than 40 minutes and equal to or lessthan 180 minutes, and particularly preferably equal to or more than 60minutes and equal to or less than 150 minutes. During this step, in acase where the by-product monohydroxy compounds are distilled offimmediately upon the generation of the by-product monohydroxy compounds,the finally obtained polycarbonate resin is low in the content of highmolecular weight components. However, in a case where the by-productmonohydroxy compounds are kept in the reaction vessel for a certainperiod of time, the finally obtained polycarbonate resin is high in thecontent of high molecular weight components.

In general, a melt polycondensation reaction is carried out in amulti-stage step of two or more stages. Specifically, a first-stagereaction is preferably carried out at a temperature of 120° C. to 260°C., and more preferably carried out at a temperature of 180° C. to 240°C., and preferably carried out under normal pressure or pressure for 0.1to 5 hours, and more preferably carried out under pressure for 0.5 to 3hours. Next, the compound represented by General Formula (1) reacts withcarbonic acid diester with a reaction temperature being increased whileincreasing the degree of decompression of the reaction system, andfinally, the polycondensation reaction is preferably carried out withthe degree of decompression of equal to or lower than 133 Pa (1 mmHg) ata temperature of 200° C. to 350° C. for 0.05 to 2 hours.

The melt polycondensation reaction may be carried out either in acontinuous manner or in a batch manner.

The reacting apparatus for use in this reaction may be a verticalreactor equipped with an anchor-type impeller, a Maxblend impeller, ahelical ribbon-type impeller or the like, may be a horizontal reactorequipped with a paddle impeller, a grid impeller, a spectacle impelleror the like, or may be an extruder-type reacting apparatus equipped witha screw. In addition, it is suitable to use a reacting apparatusconstituted of these reactors in combination as appropriate, inconsideration of the viscosity of the polymerized product.

In the polycarbonate resin according to the present embodiment, afterthe polycondensation reaction is completed, the catalyst may be removedor deactivated in order to maintain heat stability and hydrolysisstability. In general, known methods for catalyst deactivation whichinvolve addition of an acidic substance can suitably be carried out.Specific examples of an acidic substance suitable for use include esterssuch as butyl benzoate; aromatic sulfonic acids such asp-toluenesulfonic acid; aromatic sulfonic acid esters such as butylp-toluenesulfonate and hexyl p-toluenesulfonate; phosphoric acids suchas phosphorous acid, phosphoric acid and phosphonic acid; phosphorousacid esters such as triphenyl phosphite, monophenyl phosphite, diphenylphosphite, diethyl phosphite, n-propyl phosphite, n-butyl phosphite,n-hexyl phosphite, n-octyl phosphite, and mono n-octyl phosphite;phosphoric acid esters such as triphenyl phosphate, diphenyl phosphate,monophenyl phosphate, n-butyl phosphate, n-octyl phosphate, and monon-octyl phosphate; phosphonic acids such as diphenylphosphonic acid, din-octylphosphonic acid, and di n-butylphosphonic acid; phosphonic acidesters such as diethyl phenylphosphonate; phosphines such as triphenylphosphine and bis(diphenylphosphino)ethane; boric acids such as boricacid and phenylboric acid; aromatic sulfonates such asn-dodecylbenzenesulfonic acid tetra n-butylphosphonium salt; organichalides such as stearic acid chloride, benzoyl chloride, andp-toluenesulfonic acid chloride; alkyl sulfates such as dimethylsulfate; organic halides such as benzyl chloride, and the like. Each ofthese deactivating agents is preferably used in a content of 0.01 to 50times by mole and more preferably 0.3 to 20 times by mole with respectto the amount of the catalyst. In a case where the content of thedeactivating agent is less than 0.01 times by mole with respect to theamount of the catalyst, the deactivating effect is insufficient, whichis not preferable. In addition, in a case where the content of thedeactivating agent is more than 50 times by mole with respect to theamount of the catalyst, the heat resistance of the resin is lowered, andthe molded article is easily colored, which is not preferable.

After the catalyst is deactivated, a step of devolatilizing and removingcompounds having the low boiling point in the polymer at a pressure of13 to 133 Pa (0.1 to 1 mmHg) and a temperature of 200° C. to 350° C. maybe provided. In this step, a horizontal evaporator equipped with animpeller that is excellent in surface renewal ability, such as a paddleimpeller, a grid impeller, and a spectacle impeller, or a thin filmevaporator is suitable for use.

The polycarbonate resin according to the present embodiment is desiredto be extremely low in the content of contaminants, which is suitablyaccomplished by filtration of molten raw materials, filtration of thecatalyst solution, and the like. The mesh size of a filter is preferablyequal to or smaller than 5 µm, and more preferably equal to or smallerthan 1 µm. Furthermore, the generated resin is suitably filtered througha polymer filter. The mesh size of the polymer filter is preferablyequal to or smaller than 100 µm, and more preferably equal to or smallerthan 30 µm. In addition, a step of collecting resin pellets is,naturally, preferably performed in a low dust environment, and morepreferably with cleanness of equal to or less than class 1000.

[Optical Molded Article]

An optical molded article according to the present embodiment containsthe polycarbonate resin according to the present embodiment, and theoptical molded article can be produced by using the polycarbonate resinaccording to the present embodiment.

For example, the optical molded article is molded by any method such asan injection molding method, a compression molding method, an injectioncompression molding method, an extrusion molding method, or a solutioncasting method.

Since the polycarbonate resin according to the present embodiment isexcellent in moldability and heat resistance, the polycarbonate resincan be used particularly advantageously in optical lenses that arerequired to be produced by injection molding. During the molding, thepolycarbonate resin according to the present embodiment can be mixedwith other resins such as other polycarbonate resins and polyesterresins, and used.

In addition, it is possible to use various types of additives in orderto impart various characteristics in a range that does not impair theobject of the present embodiment. Examples of additives includeantioxidants, processing stabilizers, mold release agents, ultravioletabsorbers, bluing agents, polymeric metal deactivators, flameretardants, lubricants, antistatic agents, heat ray shielding agents,fluorescent dyes (including fluorescent whitening agents), pigments,light scattering agents, reinforcing fillers, surfactants, antibacterialagents, plasticizers, compatibilizers, other resins, elastomers, and thelike.

Examples of antioxidants include triethyleneglycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate],1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate],pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate],octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate,1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene,N,N-hexamethylene bis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamide),3,5-di-tert-butyl-4-hydroxy-benzyl phosphonate-diethyl ester,tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, and3,9-bis{1,1-dimethyl-2-[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]ethyl}-2,4,8,10-tetraoxaspiro(5,5)undecane,and the like.

The content of the antioxidant in the polycarbonate resin is preferably0.001 to 0.3 parts by mass with respect to 100 parts by mass of thepolycarbonate resin.

Examples of processing stabilizers include phosphorus-based processingheat stabilizers, sulfur-based processing heat stabilizers, and thelike.

Examples of phosphorus-based processing heat stabilizers includephosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid,esters thereof, and the like. Specific examples thereof includetriphenyl phosphite, tris(nonylphenyl) phosphite,tris(2,4-di-tert-butylphenyl) phosphite, tris(2,6-di-tert-butylphenyl)phosphite, tri n-decyl phosphite, tri n-octyl phosphite, tri n-octadecylphosphite, di n-decyl monophenyl phosphite, di n-octyl monophenylphosphite, diisopropyl monophenyl phosphite, mono n-butyl diphenylphosphite, monodecyl diphenyl phosphite, mono n-octyl diphenylphosphite, bis(2,6-di-tert-butyl-4-methylphenyl) pentaerythritoldiphosphite, 2,2-methylene bis(4,6-di-tert-butylphenyl) octyl phosphite,bis(n-nonylphenyl) pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, trin-butyl phosphate, triethyl phosphate, trimethyl phosphate, triphenylphosphate, diphenyl monoorthoxenyl phosphate, di n-butyl phosphate, din-octyl phosphate, diisopropyl phosphate, dimethyl benzenephosphonate,diethyl benzenephosphonate, dipropyl benzenephosphonate,tetrakis(2,4-di-t-butylphenyl)-4,4′-biphenylenediphosphonite,tetrakis(2,4-di-t-butylphenyl)-4,3′-biphenyleneiphosphonite,tetrakis(2,4-di-t-butylphenyl)-3,3′-biphenyleneiphosphonite,bis(2,4-di-tert-butylphenyl)-4-phenyl-phenylphosphonite andbis(2,4-di-tert-butylphenyl)-3-phenyl-phenylphosphonite, and the like.

The content of the phosphorus-based processing heat stabilizer in thepolycarbonate resin is preferably 0.001 to 0.2 parts by mass withrespect to 100 parts by mass of the polycarbonate resin.

Examples of sulfur-based processing heat stabilizers includepentaerythritol-tetrakis(3-laurylthiopropionate),pentaerythritol-tetrakis(3-myristylhiopropionate),pentaerythritol-tetrakis(3-stearylthiopropionate),dilauryl-3,3′-thiodipropionate, dimyristyl-3,3′-thiodipropionate,distearyl-3,3′-thiodipropionate, and the like.

The content of the sulfur-based processing heat stabilizer in thepolycarbonate resin is preferably 0.001 to 0.2 parts by mass withrespect to 100 parts by mass of the polycarbonate resin.

As a mold release agent, a mold release agent of which equal to or morethan 90% by mass is formed of esters of alcohols and fatty acids ispreferable. Specific examples of the esters of alcohols and fatty acidsinclude esters of monohydric alcohol and fatty acid and partial estersor whole esters of polyhydric alcohol and fatty acid. As the ester of amonohydric alcohol and a fatty acid, an ester of a monohydric alcoholhaving 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30carbon atoms is preferable. In addition, as the partial ester or wholeester of a polyhydric alcohol and a fatty acid, a partial ester or wholeester of polyhydric alcohol having 1 to 25 carbon atoms and saturatedfatty acid having 10 to 30 carbon atoms is preferable.

Examples of esters of a monohydric alcohol and a saturated fatty acidinclude stearyl stearate, palmityl palmitate, n-butyl stearate, methyllaurate, isopropyl palmitate, and the like. Examples of partial estersor whole esters of polyhydric alcohols and saturated fatty acids includewhole esters or partial esters of dipentaerythritol such as stearic acidmonoglyceride, stearic acid diglyceride, stearic acid triglyceride,stearic acid monosorbitate, behenic acid monoglyceride, capric acidmonoglyceride, lauric acid monoglyceride, pentaerythritol monostearate,pentaerythritol tetrastearate, pentaerythritol tetrapelargonate,propylene glycol monostearate, biphenyl biphenate, sorbitanmonostearate, 2-ethylhexyl stearate, and dipentaerythritol hexastearate.

The content of these mold release agents is preferably in a range of0.005 to 2.0 parts by mass with respect to 100 parts by mass of thepolycarbonate resin, more preferably in a range of 0.01 to 0.6 parts bymass, and even more preferably in a range of 0.02 to 0.5 parts by mass.

As the ultraviolet absorber, it is possible to include at least one typeof ultraviolet absorber selected from the group consisting of abenzotriazole-based ultraviolet absorber, a benzophenone-basedultraviolet absorber, a triazine-based ultraviolet absorber, a cyclicimino ester-based ultraviolet absorber, and a cyanoacrylate-basedultraviolet absorber. The ultraviolet absorbers listed below may be usedalone or in a combination of two or more types.

Examples of benzotriazole-based ultraviolet absorbers include2-(2-hydroxy-5-methylphenyl) benzotriazole,2-(2-hydroxy-5-tert-octylphenyl) benzotriazole,2-(2-hydroxy-3,5-dicumylphenyl) phenylbenzotriazole,2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole,2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2N-benzotriazol-2-yl)phenol], 2-(2-hydroxy-3,5-di-tert-butylphenyl) benzotriazole,2-(2-hydroxy-3,5-di-tert-butylphenyl)-5-chlorobenzotriazole,2-(2-hydroxy-3,5-di-tert-amylphenyl) benzotriazole,2-(2-hydroxy-5-tert-octylphenyl) benzotriazole,2-(2-hydroxy-5-tert-butylphenyl) benzotriazole,2-(2-hydroxy-4-n-octyloxyphenyl) benzotriazole,2,2′-methylenebis(4-cumyl-6-benzotriazolephenyl),2,2′-p-phenylenebis(1,3-benzoxazin-4-one),2-[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidomethyl)-5-methylphenyl]benzotriazole,and the like.

Examples of benzophenone-based ultraviolet absorbers include2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone,2-hydroxy-4-n-octyloxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone,2-hydroxy-4-methoxy-5-sulfoxybenzophenone,2-hydroxy-4-methoxy-5-sulfoxytrihydratebenzophenone,2,2′-dihydroxy-4-methoxybenzophenone,2,2’,4,4′-tetrahydroxybenzophenone,2,2′-dihydroxy-4,4′-dimethoxybenzophenone,2,2′-dihydroxy-4,4′-dimethoxy-5-sodium sulfoxybenzophenone,bis(5-benzoyl-4-hydroxy-2-methoxyphenyl) methane,2-hydroxy-4-n-dodecyloxybenzophenone,2-hydroxy-4-methoxy-2′-carboxybenzophenone, and the like.

Examples of triazine ultraviolet absorbers include2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[(n-hexyl)oxy]-phenol,2-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-[(n-octyl)oxy]-phenol, and the like.

Examples of cyclic imino ester-based ultraviolet absorbers include2,2′-bis(3,1-benzoxazin-4-one),2,2′-p-phenylenebis(3,1-benzoxazine-4-one),2,2′-m-phenylenebis(3,1-benzoxazin-4-one),2,2′-(4,4′-diphenylene)bis(3,1-benzoxazin-4-one),2,2′-(2,6-naphthalene)bis(3,1-benzoxazin-4-one), 2,2‘-(1,5-naphthalene)bis(3,1-benzoxazine-4-one),2,2′-(2-methyl-p-phenylene)bis(3,1-benzoxazin-4-one), 2,2‘-(2-nitro-p-phenylene)bis(3,1-benzoxazin-4-one) and2,2′-(2-chloro-p-phenylene)bis(3,1-benzoxazin-4-one), and the like.

Examples of cyanoacrylate-based ultraviolet absorbers include1,3-bis-[(2′-cyano-3’,3′-diphenylacryloyl)oxy]-2,2-bis[[(2-cyano-3,3-diphenylacryloyl)oxy]methyl]propane,and 1,3-bis-[(2-cyano-3,3-diphenylacryloyl)oxy]benzene, and the like.

The content of the ultraviolet absorber is preferably 0.01 to 3.0 partsby mass with respect to 100 parts by mass of the polycarbonate resin,and more preferably 0.02 to 1.0 part by mass, and even more preferably0.05 to 0.8 parts by mass. With this blending amount range, it ispossible to impart sufficient weather resistance to a polycarbonateresin according to the application thereof.

Examples of bluing agents include Macrolex Violet B and Macrolex Blue RRmade by Bayer, and Polysynthren Blue RLS made by Clariant, and the like.

The bluing agent is effective to eliminate the yellowness of thepolycarbonate resin. In particular, in a case of a polycarbonate resinto which weather resistance is imparted, a certain amount of ultravioletabsorber is blended, thus, the polycarbonate resin molded article tendsto be slightly yellow due to the “action and color of the ultravioletabsorber” and blending a bluing agent therein is particularly effectivefor imparting natural transparency to a sheet or lens.

The blending amount of the bluing agent is, for example, preferably 0.05to 1.5 ppm with respect to the polycarbonate resin, and more preferably0.1 to 1.2 ppm.

The polycarbonate resin according to the present embodiment exhibits ahigh refractive index and excellent heat resistance, and has a fluiditysuitable for molding. Furthermore, since optical distortion is unlikelyto occur due to a low degree of birefringence, the optical moldedarticle can be advantageously used, as an optical molded article, notonly for optical lenses, but also as an electrically conductivetransparent substrate for use in liquid crystal displays, organic ELdisplays, solar photovoltaic cells, and the like, and suitable for useas a structural material or functional material for optical componentssuch as optical disks, liquid crystal panels, optical cards, sheets,films, optical fibers, connectors, evaporated plastic reflectingmirrors, displays, and the like.

A surface of such an optical molded article may be provided with acoating layer such as an antireflection layer or a hard coat layer, asnecessary. Such an antireflection layer may be constituted of a singlelayer or multiple layers, and may be formed of an organic material or aninorganic material, but is preferably formed of an inorganic material.Specific examples include oxides or fluorides such as silicon oxide,aluminum oxide, zirconium oxide, titanium oxide, cerium oxide, magnesiumoxide, magnesium fluoride, and the like.

(Optical Lens)

An optical lens produced by using the polycarbonate resin according tothe present embodiment is very useful since the optical lens has a highrefractive index and are excellent in heat resistance, and thus can beused in the fields of telescopes, binoculars, television projectors, andothers where expensive high refractive index glass lenses have been usedin the related art. The optical lens is preferably used in the form ofan aspherical lens, as necessary. In the case of the aspherical lens, asingle lens achieves substantially zero spherical aberration, whicheliminates the need to remove spherical aberration by combining aplurality of spherical lenses, so that light weight and production costsavings can be achieved. Therefore, an aspherical lens is particularlyuseful as a camera lens among optical lenses.

The optical lens according to the present embodiment is molded by anymethod such as an injection molding method, a compression moldingmethod, or an injection compression molding method. According to thepresent embodiment, an aspherical lens with a high refractive index anda low degree of birefringence can be obtained in a simpler manner, whichis technically difficult to process in the case of using glass lenses.

(Optical Film)

An optical film produced by using the polycarbonate resin according tothe present embodiment is excellent in transparency and heat resistance,and is therefore suitable for use in films for liquid crystalsubstrates, optical memory cards, and the like.

As described above, the embodiments of the present invention have beendescribed, but these are examples of the present invention, and variousconfigurations other than the above can be adopted.

EXAMPLES

Hereinafter, the present embodiment will be described in detail withreference to Examples and Comparative Examples. The present embodimentis not limited to the description of these examples.

1. Measurement and Evaluation Method

In the following Examples and Comparative Examples, the measurement andevaluation of each physical property were performed by the followingmethod.

1) Weight average molecular weight (Mw) in terms of polystyrene: Gelpermeation chromatography (GPC, manufactured by Waters Corporation,1515, 2414, and 2489) was used to prepare a calibration curve frompolystyrene standards of known molecular weight (molecular weightdistribution = 1) by using chloroform as an eluate. Based on thiscalibration curve, Mw was calculated from the retention time in GPC.

2) Refractive index (n633): a silicon wafer was coated with a chloroformsolution of a resin having a concentration of 8.5 wt% by using a spincoater at 200 rpm for 20 seconds and 1000 rpm for 5 seconds, and bakedat 120° C. for 5 minutes and 200° C. for 2 minutes to adjust a sample,and a refractive index and a thickness of a film were calculated byfitting the following optical model to optical measurement data at awavelength of 200 to 1000 nm by using a spectroscopic ellipsometer GES5E(manufactured by Semilab Semiconductor Physics Laboratory Co., Ltd.) .

(Optical Model)

-   Laminated structure: Film/SiO₂ (thickness of 2 nm) /Si substrate    (thickness of 500 µm)-   Dispersion type of film: Cauchy + Lorentz oscillator model

3) Glass transition temperature (Tg): Measurement is carried out by adifferential scanning calorimetry (DSC: DSC-60 manufactured by ShimadzuCorporation).

1. Preparation of Compound Represented by Formula (1) (Example 1)Synthesis of 9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluoreneStep (I): Synthesis of 9,9-bis(2′-hydroxyethyl)-2,7-dibromo-9H-fluorene

A 500 ml flask was charged with 66.5 g (0.2 mol) of2,7-dibromo-9H-fluorene, 56 g (0.998 mol) of potassium hydroxide(powder), 3.4 g (0.02 mol) of potassium iodide, 150 ml of dimethylsulfoxide, and cooled to 10° C. with ice water. Thereafter, 58.4 g(0.467 mol) of 2-bromoethanol was added dropwise over 45 minutes, andthe mixture was then stirred overnight at room temperature. Thereafter,the reaction solution was heated to 50° C. and heated and stirred for 40hours. The reaction mixture was discharged into 2 liters of distilledwater and pH was adjusted to 6 with concentrated hydrochloric acid. Theobtained solid was filtered and separated, and washed with 3 liters ofwater. The obtained solid was dissolved in 1 liter of ethyl acetate,washed with 500 ml of distilled water, and concentrated with anevaporator, and chloroform was added to obtain 34.8 g of9,9-bis(2′-hydroxyethyl)-2,7-dibromo-9H-fluorene as colorless crystals.

Step (II): Preparation of9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene

A 1-liter flask was charged with 20.75 g (50 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-dibromo-9H-fluorene, 19.17 g (0.11 mol) ofnaphthalene-2-boronic acid, 15.3 g (0.11 mol) of potassium carbonate,250 g of distilled water, and 400 g of dimethyl sulfoxide. 3.0 g oftetrakis(triphenylphosphine) palladium was added to this reactionmixture, the mixture was heated to 100° C., and heated and stirred for 5hours. After cooling, the produced solid was filtered and separated,washed with 500 g of water, and vacuum dried at 50° C. After drying, thesolid was suspended and washed with chloroform to obtain 20.87 g of9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene as colorlesscrystals. The melting point measured by DSC was 236° C.

(Example 2) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene Step (I):Synthesis of 2-(2′-bromoethoxy)tetrahydropyran

A 2-liter round bottomed flask equipped with a stirrer, a thermometerand a dropping funnel was charged with 150 g (1.20 mol) of2-bromoethanol and 800 ml of dichloromethane, and cooled with ice water.Thereafter, when the internal temperature reached 5° C., 130 g (1.56mol) of 3,4-dihydro-2H-pyran was added dropwise at equal to or lowerthan 10° C. After completion of the dropwise addition, 30 g (0.12 mol)of pyridinium p-toluenesulfonate was added, and the mixture was stirredovernight at room temperature. Thereafter, saturated water of sodiumhydrogencarbonate was added, and a dichloromethane layer was washed withwater. The obtained dichloromethane layer was concentrated by anevaporator to obtain 255 g of 2-(2′-bromoethoxy)tetrahydropyran as apale yellow oil.

Step (II): Synthesis of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dibromo-9H-fluorene

A 2-liter round bottomed flask equipped with a stirrer, a thermometerand a reflux tube was charged with 255 g of2-(2′-bromoethoxy)tetrahydropyran, 270 ml of toluene, and 164 g (0.506mol) of 2,7-dibromo-9H-fluorene, and 270 ml of an aqueous solution of50% sodium hydroxide were added thereto. Thereafter, 8.5 g (26.2 mmol)of tetrabutylammonium bromide was added, the mixture was heated to 100°C., and the mixture was heated and stirred for 11.5 hours. Thereafter,the reaction mixture was cooled to room temperature, an aqueous layerwas separated, 700 ml of ethyl acetate and 700 ml of distilled waterwere then added, and the mixture was washed with water. After thewashing with water was repeatedly carried out, a layer formed of ethylacetate and toluene was separated and concentrated by an evaporator. Asmall amount of seed crystals of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dibromo-9H-fluorene wasadded to a viscous liquid obtained after concentration, and methanol wasadded to carry out crystallization. The obtained crystals was filtered,washed with a small amount of methanol, and then recrystallized byheating from 500 ml of methanol to obtain 246 g of9,9-bis[2-(2′-tetrahydropyranyl) ethoxy]-2,7-dibromo-9H-fluorene ofpurpose was obtained as pale yellow crystals.

-   m. p. 98.5° C.-   ¹H-NMR (CDC13) δ1.30-1.53 (m, 12H) 2.34-2.38 (t, 4H) 2.70-3.5 (m,    8H) 4.1 (t), 2H), 7.43-7.55 (m, 6H)

Step (III): Synthesis of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene

A 1-liter round bottomed flask equipped with a stirrer, a thermometerand a reflux tube was charged with 72.55 g (125 mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dibromo-9H-fluorene, 475ml of toluene, 61 g (442 mmol) of potassium carbonate, 47.29 g (275mmol) of 2-naphthalene boronic acid, and 211 ml of distilled water, and1.4 g of tetrakis(triphenylphosphine)palladium were added to thisreaction mixture while being stirred, and then the resultant mixture washeated up to 80° C. The mixture was heated and stirred at 80° C. for 12hours, and then cooled to room temperature. After separating the aqueouslayer, a toluene layer was washed with distilled water, and then thetoluene layer was concentrated by an evaporator. 730 ml of methanol wasadded to the concentrated residue, and the resultant solid was filteredand separated, and washed with methanol. Thereafter, purification wascarried out by silica gel column chromatography (eluent toluene totoluene/ethyl acetate = 9/1), and then recrystallization from methylcellosolve was carried out to obtain 121.01 g of a desired product.Yield 72%, HPLC purity 99.3%, m. p. 148° C.,

¹H-NMR (CDCl₃) δ1.20-1.70 (m, 12H), 2, 55 (t, 4H), 2.8-3.5 (m, 8H), 4.16(m, 2H), 7.40-7.65 (m, 4H), 7.70-8.05 (m, 14H), 8.1 (s, 2H)

Step (IV): Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene

A 1-liter round bottomed flask equipped with a stirrer, a thermometerand a reflux tube was charged with 60.00 g (88.9 mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid, the temperature was increased to 115° C.with stirring, and the mixture was heated and stirred at the sametemperature for 4 hours. Thereafter, the mixture was cooled to roomtemperature, 180 ml of water was added, and the resulting crystals werefiltered and separated. The obtained crystals were washed with distilledwater, dried under reduced pressure at 50° C., and then suspended andwashed with hot methyl cellosolve to obtain 38.73 g of a desiredproduct. Yield 85%, m. p. 249.5° C.,

¹H-NMR (DMSO-d₆) δ2.43 (t, 4H), 2.80 (t, 4H), 4.16 (t, 2H), 7.50-7.60(m, 4H), 7.8-8.1 (m, 12H), 8.35 (s, 2H)

(Example 3) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluorene

66.05 g of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluorenewas obtained according to the operations described in the step (iii) ofExample 2, except that 58.85 g (275 mmol) of dibenzo[b,d]furan-4-ylboronic acid was used instead of using 47.29 g (275 mmol) of2-naphthalene boronic acid in the step (iii) of Example 2. Yield 70%,HPLC purity 97.5%, m. p. 176.7° C.,

¹H-NMR (CDCl₃) δ1.29-1.45 (10H, m), 1.58 (2H, m), 2.58 (4H, t), 2.98(2H, q), 3.24 (2H, dt), 3.40 (2H, q), 3.55 (2H, dt), 4.23 (2H, s), 7.39(2H, t), 7.48 (4H, q), 7.64 (2H, d), 7.68-7.71 (2H, m), 7.90-8.03 (10H,m)

41.03 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 60.00 g (79.4 mmol)of 9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluorene,540 ml of methyl cellosolve, 22 ml of distilled water, and 6.2 ml ofconcentrated hydrochloric acid were used instead of using 60.00 g (88.9mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid in the step (iv) of Example 2. Yield 88%,HPLC purity 99.4%, m. p. 247.4° C.,

¹H-NMR (DMSO-d₆) δ2.40 (4H, t), 2.98 (4H, m), 4.24 (2H, t), 7.46 (2H,t), 7.58 (4H, dt), 7.82 (4H, dd), 8.03-8.10 (6H, m), 8.22 (4H, dd)

(Example 4) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-bis[4-(naphthalen-2-yl-)phenyl]-9H-fluorene

68.23 g of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[4-(naphthalen-2-yl-)phenyl]-9H-fluorenewas obtained according to the operations described in the step (iii) ofExample 2, except that 68.22 g (275 mmol) of 4-(naphthalen-2-yl)phenylboronic acid was used instead of using 47.29 g (275 mmol) of2-naphthalene boronic acid in the step (iii) of Example 2. Yield 66%,HPLC purity 99.2%, m. p. 209.4° C.,

¹H-NMR (CDCl₃) δ1.26-1.61 (12H, m), 2.55 (4H, t), 2.86 (2H, q),3.22-3.32 (4H, m), 3.51-3.56 (2H, m), 4.17 (2H, t), 7.49-7.55 (4H, m),7.67 (2H, d), 7.75 (2H, d), 7.78-7.82 (6H, m), 7.84-7.90 (8H, m), 7.95(4H, t), 8.13 (2H, s)

41.10 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 60.00 g of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[4-(naphthalen-2-yl-)phenyl]-9H-fluorene,500 ml of methyl cellosolve, 20 ml of distilled water, and 6 ml ofconcentrated hydrochloric acid were used instead of using 60.00 g (88.9mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid in the step (iv) of Example 2. Yield 86%,HPLC purity 99.6%, m. p. 341.3° C.,

¹H-NMR (DMSO-d₆) δ2.41 (4H, t), 2.83 (4H, q), 4.20 (2H, t), 7.53-7.60(4H, m), 7.83 (2H, d), 7.94-8.00 (16H, m), 8.06 (4H, d), 8.33 (2H, s)

(Example 5) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-bis[3-(naphthalen-2-yl-)phenyl]-9H-fluorene

70.30 g of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[3-(naphthalen-2-yl-)phenyl]-9H-fluorenewas obtained according to the operations described in the step (iii) ofExample 2, except that 68.22 g (275 mmol) of 3-(naphthalen-2-yl)phenylboronic acid was used instead of using 47.29 g (275 mmol) of2-naphthalene boronic acid in the step (iii) of Example 2. Yield 68%,HPLC purity 98.9%, m. p. 171.6° C.,

¹H-NMR (CDCl₃) δ1.26-1.58 (12H, m), 2.54 (4H, t), 2.86 (2H, q),3.22-3.30 (4H, m), 3.49-3.54 (2H, m), 4.16 (2H, t), 7.51-7.61 (6H, m),7.66-7.74 (8H, m), 7.81 (2H, d), 7.84 (2H, dd), 7.90 (2H, d), 7.94-7.99(6H, m), 8.14 (2H, s)

41.58 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 60.00 g (72.5 mmol)of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[3-(naphthalen-2-yl-)phenyl]-9H-fluorene,500 ml of methyl cellosolve, 20 ml of distilled water, and 5.7 g ofconcentrated hydrochloric acid were used instead of using 60.00 g (88.9mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid in the step (iv) of Example 2. Yield 87%.The final product was purified by column chromatography (eluent: ethylacetate/chloroform = ⅛ -> ¼). HPLC purity 99.7%, m. p. 143.1° C.,

¹H-NMR (DMSO-d₆) δ: 2.52 (4H, t), 3.17 (4H, q), 7.51-7.54 (4H, m), 7.60(2H, t), 7.67-7.69 (2H, m), 7.74 (2H, dd), 7.76 (2H, s), 7.82-7.91 (6H,m), 7.94-7.99 (6H, m), 8.14 (2H, s)

(Example 6) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-diphenanthren-9″-yl-9H-fluorene

73.62 g of 9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-diphenanthrene9″-yl-9H-fluorene was obtained according to the operations described inthe step (iii) of Example 2, except that 61.06 g (275 mmol) ofphenanthren-9-yl boronic acid was used instead of using 47.29 g (275mmol) of 2-naphthalene boronic acid in the step (iii) of Example 2.Yield 76%, HPLC purity 95.9%, viscous solid,

¹H-NMR (CDCl₃) δ1.36-1.64 (12H, m), 2.50 (4H, t), 2.99 (2H, q),3.30-3.43 (4H, m), 3.58 (2H, dt), 4.29 (2H, s), 7.57 (4H, d), 7.63-7.72(8H, m), 7.77 (2H, s), 7.90 (2H, d), 7.93-7.95 (2H, m), 8.03 (2H, d),8.79 (4H, dd)

48.22 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 70.00 g (90.3 mmol)of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-diphenanthren-9″-yl-9H-fluorene,610 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid were used instead of using 60.00 g (88.9mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid in the step (iv) of Example 2. Yield 88%.The final product was purified by column chromatography (eluent: ethylacetate/chloroform = ⅙ -> ¼). HPLC purity 99.3%, m. p. 226.9° C.,

¹H-NMR (DMSO-d₆) δ2.48 (4H, t), 3.31 (4H, q), 7.57-7.73 (12H, m), 7.77(2H, s), 7.95 (6H, dd), 8.79 (4H, dd)

(Example 7) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]thiophen-4″-yl]-9H-fluorene

68.87 g of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[dibenzo[b,d]thiophen-4″-y1]-9H-fluorenewas obtained according to the operations described in the step (iii) ofExample 2, except that 62.72 g (275 mmol) of dibenzo[b,d]thiophen-4-ylboronic acid was used instead of using 47.29 g (275 mmol) of2-naphthalene boronic acid in the step (iii) of Example 2. Yield 70%,HPLC purity 99.1%, viscous solid,

¹H-NMR (CDCl₃) δ1.28-1.43 (10H, m), 1.55 (2H, m), 2.56 (4H, t), 2.95(2H, q), 3.22 (2H, dt), 3.37 (2H, q), 3.52 (2H, dt), 4.20 (2H, s), 7.51(2H, t), 7.68 (4H, q), 7.85 (2H, d), 7.82-7.89 (2H, m), 8.11-8.24 (10H,m)

40.10 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 60.00 g (76.4 mmol)of 9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[dibenzo[b,d]thiophen-4″-yl]-9H-fluorene,500 ml of methyl cellosolve, 20 ml of distilled water, and 6.0 ml ofconcentrated hydrochloric acid were used instead of using 60.00 g (88.9mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid in the step (iv) of Example 2. Yield 85%,HPLC purity 98.9%, m. p. 223.6° C.,

¹H-NMR (DMSO-d₆) δ2.38 (4H, t), 2.93 (4H, dt), 4.26 (2H, t), 7.57 (4H,dd), 7.69-7.71 (4H, m), 7.79 (2H, d), 7.97 (2H, s), 8.04 (2H, dd), 8.10(2H, d), 8.43-8.47 (4H, dd)

(Example 8) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-bis[4″-phenoxyphenyl]-9H-fluorene

68.31 g of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[4-phenoxyphenyl]-9H-fluorenewas obtained according to the operations described in the step (iii) ofExample 2, except that 58.86 g (275 mmol) of 4-phenoxyphenyl boronicacid was used instead of using 47.29 g (275 mmol) of 2-naphthaleneboronic acid in the step (iii) of Example 2. Yield 72%, HPLC purity98.8%, viscous solid,

¹H-NMR (CDCl₃) δ1.24-1.59 (12H, m), 2.48 (4H, t), 2.81 (2H, q),3.20-3.27 (4H, m), 3.48-3.54 (2H, m), 4.14 (2H, t), 7.07-7.15 (10H, m),7.37 (4H, dt), 7.55 (2H, d), 7.60-7.63 (6H, m), 7.74 (2H, d)

38.29 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 60.00 g (79.1 mmol)of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[4″-phenoxyphenyl]-9H-fluorene,530 ml of methyl cellosolve, 22 ml of distilled water, and 6.2 ml ofconcentrated hydrochloric acid were used instead of using 60.00 g (88.9mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid in the step (iv) of Example 2. Yield 82%,HPLC purity 99.7%, m. p. 134.1° C.,

¹H-NMR (DMSO-d₆) δ2.34 (4H, t), 2.76 (4H, q), 4.14 (2H, t), 7.07-7.20(10H, m), 7.43 (4H, t), 7.67 (2H, dd), 7.81 (6H, t), 7.90 (2H, d)

(Example 9) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-bis[4″-phenylnaphthalen-1″-y1]-9H-fluorene

73.4 g of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[4″-phenylnaphthalen-1″-yl-]-9H-fluorenewas obtained according to the operations described in the step (iii) ofExample 2, except that 68.22 g (275 mmol) of 4-phenylnaphthalen-1-ylboronic acid was used instead of using 47.29 g (275 mmol) of2-naphthalene boronic acid in the step (iii) of Example 2. Yield 71%,HPLC purity 99.8%, m. p. 230.3° C.,

¹H-NMR (CDCl₃) δ1.36-1.61 (12H, m), 2.50 (4H, t), 2.97 (2H, q), 3.30(2H, dt), 3.38 (2H, q), 3.57 (2H, dt), 4.27 (2H, s), 7.45-7.58 (20H, m),7.66 (2H, s), 7.89 (2H), d), 7.98-8.00 (2H, m), 8.05-8.10 (2H, m)

47.95 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 70.00 g (84.6 mmol)of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[4″-phenylnaphthalen-1″-yl-]-9H-fluorene,570 ml of methyl cellosolve, 24 ml of distilled water, and 7.0 ml ofconcentrated hydrochloric acid were used instead of using 60.00 g (88.9mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid in the step (iv) of Example 2. Yield 86%,HPLC purity 99.0%, m. p. 271.4° C.,

¹H-NMR (DMSO-d₆) δ2.34 (4H, t), 2.95 (4H, dt), 4.24 (2H, t), 7.51-7.63(20H, m), 7.72 (2H, s), 7.90-7.93 (2H, m), 7.99-8.01 (2H, m), 8.08 (2H,d)

(Example 10) Synthesis of9,9-bis(2′-hydroxyethyl)-2,7-bis[9″,9″-dimethyl-9″H-fluoren-2″-yl]-9H-fluorene

76.67 g of 9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[9″,9″-dimethyl-9″H-fluoren-2″-yl]-9H-fluorenewas obtained according to the operations described in the step (iii) ofExample 2, except that 65.47 g (275 mmol) of9,9-dimethyl-9H-fluoren-2-yl boronic acid was used instead of using47.29 g (275 mmol) of 2-naphthalene boronic acid in the step (iii) ofExample 2. Yield 76%, HPLC purity 91.0%, viscous solid,

¹H-NMR (CDCl₃) δ1.25-1.50 (12H, m), 1.58 (12H, s), 2.56 (4H, t), 2.87(2H, q), 3.23-3.32 (4H, m), 3.51-3.57 (2H, m), 4.16 (2H, t), 7.32-7.39(4H, m), 7.47 (2H, dd), 7.62-7.67 (4H, m), 7.69-7.72 (4H, m), 7.76-7.82(6H, m)

48.21 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 70.00 g (89.7 mmol)of 9,9-bis [2-(2′-tetrahydropyranyloxy)ethyl]-2,7-bis[9″,9″-dimethyl-9″H-fluoren-2″-yl]-9H-fluorene, 590 ml of methyl cellosolve,24 ml of distilled water, and 6.8 ml of concentrated hydrochloric acidwere used instead of using 60.00 g (88.9 mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorene,600 ml of methyl cellosolve, 25 ml of distilled water, and 7 ml ofconcentrated hydrochloric acid in the step (iv) of Example 2. Yield 87%,HPLC purity 96.9%, m. p. 272.3° C.,

¹H-NMR (DMSO-d₆) δ1.55 (12H, s), 2.42 (4H, t), 2.79 (4H, m), 4.18 (2H,t), 7.33-7.40 (4H, m), 7.59 (2H, dd), 7.76-7.79 (4H, m), 7.88 (2H, d),7.95 (8H, dd)

(Example 11) Synthesis of 9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-1″yl-9H-fluorene

65.80 g of 9,9-bis [2(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthyl-1″-yl-9H-fluorene wasobtained according to the operations described in the step (iii) ofExample 2, except that 47.29 g (275 mmol) of 1-naphthalene boronic acidwas used instead of using 47.29 g (275 mmol) of 2-naphthalene boronicacid in the step (iii) of Example 2. Yield 78%, HPLC purity 91.0%,viscous solid,

¹H-NMR (CDCl₃) δ1.14-1.46 (m, 12H), 2.47 (t, 4H), 2.9-3.6 (m, 8H), 4.2(s, 2H), 7.5-8.1 (m, 20H)

35.13 g of a desired product was obtained according to the operationsdescribed in the step (iv) of Example 2, except that 60.00 g (88.9 mmol)of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-1″yl-9H-fluorenewas used instead of using 60.00 g (88.9 mmol) of9,9-bis[2-(2′-tetrahydropyranyloxy)ethyl]-2,7-dinaphthalen-2″-yl-9H-fluorenein the step (iv) of Example 2. Yield 78%, HPLC purity 95.4%, viscoussolid,

¹H-NMR (DMSO-d₆) δ2.3 (t, 4H), 2.9 (t, 4H), 4.2 (2, 2H), 7.5-8.2 (m,20H)

(Comparative Synthesis Example 1)

19.9 g of 9,9-bis(2′-hydroxyethyl)-2,7-didiphenyl-9H-fluorene wasobtained as colorless crystals according to the operations described inExample 1, except that 13.41 g (0.11 mol) of phenyl boronic acid wasused instead of using 19.17 g (0.11 mol) of naphthalene-2-boronic acidin Example 1.

2. Production of Polycarbonate Resin (Example 12)

A reactor equipped with a distiller was charged with 20.26 g (40 mmol)of 9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene obtainedin Example 1, 8.56 g (40 mmol) of diphenylcarbonate (hereinafter,abbreviated as “DPC” in some cases), and 15 µL (3 × 10⁻⁶ mol) of a 0.02M-sodium hydrogencarbonate aqueous solution, and the mixture reacted at240° C. and 100 kPa for one hour. Thereafter, the degree ofdecompression was adjusted to 19 kPa, and the mixture reacted for 20minutes. Then, the mixture reacted at the same temperature and the samepressure for 70 minutes. Next, the degree of decompression was adjustedto 16 kPa and the mixture reacted for 20 minutes, and the degree ofdecompression was further adjusted to 13 kPa and the mixture reacted for20 minutes. Thereafter, when the degree of decompression was reduced to130 Pa for 40 minutes and reached a predetermined torque through thereaction at the same pressure for 30 minutes, the vacuum was releasedwith nitrogen gas to extract the polycarbonate resin.

A weight average molecular weight (Mw) of the obtained polycarbonateresin was 32300, and a Tg was 135° C.

A refractive index (n633) of this polycarbonate resin was 1.7608.

(Comparative Example 2)

A polycarbonate resin was obtained according to the operations inExample 12, except that in Example 12, 16.26 g (40 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-diphenyl-9H-fluorene was used instead ofusing 20.26 g (40 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene obtained inExample 1.

A weight average molecular weight (Mw) of the obtained polycarbonateresin was 28300, and a Tg was 112° C.

A refractive index (n633) of this polycarbonate resin was 1.6959.

(Example 13)

A reactor equipped with a distiller was charged with 20.26 g (40 mmol)of 9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″-yl-9H-fluorene obtainedin Example 2, 8.56 g (40 mmol) of diphenylcarbonate, and 15 µL (3 × 10⁻⁶mol) of a 0.02 M-sodium hydrogencarbonate aqueous solution, and themixture reacted at 260° C. and 100 kPa for 20 minutes and at 270° C. and100 kPa for 30 minutes. Thereafter, the degree of decompression wasadjusted to 22 kPa, and the mixture reacted for 20 minutes. Then, themixture reacted at the same temperature and the same pressure for 60minutes. Next, the degree of decompression was adjusted to 16 kPa andthe mixture reacted for 20 minutes, and the degree of decompression wasfurther adjusted to 13 kPa and the mixture reacted for 20 minutes.Thereafter, when the degree of decompression was reduced to 130 Pa for40 minutes and reached a predetermined torque through the reaction atthe same pressure for 30 minutes, the vacuum was released with nitrogengas to extract the polycarbonate resin.

The obtained polycarbonate resin had a weight average molecular weight(Mw) of 4250, and was a crystalline polymer having a Tg of 115° C. and aTm of 172° C. (calorific value: 1.87 J/g).

A refractive index (n633) of this polycarbonate resin was 1.7708.

(Example 14)

A reactor equipped with a distiller was charged with 23.46 g (40 mmol)of 9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluoreneobtained in Example 3, 8.56 g (40 mmol) of DPC, and 15 µL (3 × 10⁻⁶ mol)of a 0.02 M-sodium hydrogencarbonate aqueous solution, and the mixturereacted at 240° C. and 100 kPa for one hour. Thereafter, the degree ofdecompression was adjusted to 22 kPa and the mixture reacted for 20minutes, and the degree of decompression was further adjusted to 13 kPaand the mixture reacted for 20 minutes. Thereafter, when the degree ofdecompression was reduced to 130 Pa for 40 minutes and reached apredetermined torque through the reaction at the same pressure for 30minutes, vacuum was released with nitrogen gas to extract thepolycarbonate resin.

A weight average molecular weight (Mw) of the obtained polycarbonateresin was 8430, and a Tg was 118° C.

A refractive index (n633) of this polycarbonate resin was 1.730.

(Example 15)

A polycarbonate resin was produced according to the operations inExample 14, except that in Example 14, 26.35 g (40 mmol) of9,9-bis(2′-dihydroxyethyl)-2,7-bis[3-(naphthalen-2-yl-)phenyl]-9H-fluoreneobtained in Example 5 was used instead of using 23.46 g (40 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluoreneobtained in Example 3.

A weight average molecular weight (Mw) of the obtained polycarbonateresin was 5240, and a Tg was 105° C.

A refractive index (n633) of this polycarbonate resin was 1.735.

(Example 16)

A polycarbonate resin was produced according to the operations inExample 14, except that in Example 14, 24.27 g (40 mmol) of 9,9-bis(2′-dihydroxyethyl) -2,7-diphenanthren-9″-yl-9H-fluorene obtained inExample 6 was used instead of using 23.46 g (40 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluoreneobtained in Example 3.

A weight average molecular weight (Mw) of the obtained polycarbonateresin was 5550, and a Tg was 126° C.

A refractive index (n633) of this polycarbonate resin was 1.718.

(Example 17)

A polycarbonate resin was produced according to the operations inExample 14, except that in Example 14, 23.63 g (40 mmol) of 9,9-bis(2′-dihydroxyethyl)-2,7-bis (4″-phenoxyphenyl)-9H-fluorene obtained inExample 8 was used instead of using 23.46 g (40 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluoreneobtained in Example 3.

A weight average molecular weight (Mw) of the obtained polycarbonateresin was 4870, and a Tg was 67° C.

A refractive index (n633) of this polycarbonate resin was 1.715.

(Example 18)

A polycarbonate resin was produced according to the operations inExample 14, except that in Example 14, 26.35 g (40 mmol) of9,9-bis(2′-dihydroxyethyl)-2,7-bis(4″-phenylnaphthalen-1″-yl)-9H-fluoreneobtained in Example 9 was used instead of using 23.46 g (40 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-bis[dibenzo[b,d]furan-4″-yl]-9H-fluoreneobtained in Example 3.

The obtained polycarbonate resin had a weight average molecular weight(Mw) of 6170, and was a crystalline polymer having a Tg of 122° C. and aTm of 273° C. (calorific value: 8.82 J/g).

A refractive index (n633) of this polycarbonate resin was 1.796.

(Example 19)

A reactor equipped with a distiller was charged with 4.04 g (8 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″yl-9H-fluorene obtained inExample 2, 10.52 g (24 mmol) of9,9-bis[4′-(2″-hydroxyethoxy)phenyl]-9H-fluorene, 1.32 g (8 mmol) ofbisphenol A, 8.57 g (40 mmol) of DPC, and 15 µL (3 × 10⁻⁶ mol) of a 0.02M-sodium hydrogencarbonate aqueous solution, and the mixture reacted at240° C. and 100 kPa for one hour. Thereafter, the degree ofdecompression was adjusted to 22 kPa and the mixture reacted for 20minutes, and the degree of decompression was further adjusted to 13 kPaand the mixture reacted for 20 minutes. Thereafter, when the degree ofdecompression was reduced to 130 Pa for 40 minutes and reached apredetermined torque through the reaction at the same pressure for 30minutes, vacuum was released with nitrogen gas to extract thepolycarbonate resin.

A weight average molecular weight (Mw) of the obtained polycarbonateresin was 32500, and a Tg was 139° C.

A refractive index (n633) of this polycarbonate resin was 1.713.

In addition, the total transmittance of a sheet that is formed of thepolycarbonate resin heat-pressed at 250° C. and has a thickness of 500µm was 82%.

(Example 20)

A reactor equipped with a distiller was charged with 4.00 g (6 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-bis[4-(naphthalen-2-yl-)phenyl]-9H-fluoreneobtained in Example 4, 7.98 g (18 mmol) of9,9-bis[4′-(2″-hydroxyethoxy)phenyl]-9H-fluorene, 1.39 g (6 mmol) ofbisphenol A, 6.55 g (30 mmol) of DPC, and 10 µL (2 × 10⁻⁶ mol) of a 0.02M-sodium hydrogencarbonate aqueous solution, and the mixture reacted at270° C. and 100 kPa for one hour. Thereafter, the degree ofdecompression was adjusted to 22 kPa and the mixture reacted for 20minutes, and the degree of decompression was further adjusted to 13 kPaand the mixture reacted for 20 minutes. Thereafter, when the degree ofdecompression was reduced to 130 Pa for 40 minutes and reached apredetermined torque through the reaction at the same pressure for 70minutes, vacuum was released with nitrogen gas to extract thepolycarbonate resin.

A weight average molecular weight (Mw) of the obtained polycarbonateresin was 27800, and a Tg was 157° C. The appearance of thepolycarbonate resin was colorless and transparent.

(Example 21)

A reactor equipped with a distiller was charged with a mixture formed of3.0375 g (6 mmol) of9,9-bis(2′-hydroxyethyl)-2,7-dinaphthalen-2″yl-9H-fluorene obtained inExample 2, 6.1380 g (14 mmol) of9,9-bis[4′-(2″-hydroxyethoxy)phenyl]-9H-fluorene, 4.8850 g (8 mmol) of2,6-naphthalene dicarboxylic acid dimethyl ester, and 3.7 µl (50 ppm asTi) of titanium tetraisopropoxide, and the mixture reacted at 280° C.and 100 kPa for one hour. Thereafter, the degree of decompression wasadjusted to 20 kPa and the mixture reacted for 20 minutes, and thedegree of decompression was further adjusted to 13 kPa and the mixturereacted for 20 minutes. Thereafter, when the degree of decompression wasreduced to 130 Pa for 30 minutes and reached a predetermined torquethrough the reaction at the same pressure for 30 minutes, vacuum wasreleased with nitrogen gas to extract the polyester resin.

A weight average molecular weight (Mw) of the obtained polyester resinwas 6300, and a Tg was 118° C.

As described above, it can be understood that the polycarbonate resinobtained from the compound represented by General Formula (1) accordingto the present embodiment has a high refractive index.

1. A compound represented by General Formula (1),

wherein in General Formula (1), Ar₁ and Ar₂ independently represent agroup selected from the following formulae,

where, R₁ to R₆ each represent a hydrogen atom, a hydrocarbon group, ora heteroatom-containing hydrocarbon group, A₁ to A₅ and B₁ to B₅ eachrepresent a hydrogen atom, a hydrocarbon group, or aheteroatom-containing hydrocarbon group, at least one of A₁ to A₅ is a—Y₁—Ar₃ group, at least one of B₁ to B₅ is a —Y₂—Ar₄ group, Y₁ and Y₂each represent a single bond or a linking group, Ar₃ and Ar₄ eachrepresent an aromatic group, X₁ to X₄ each are —O—, —S—, —NR′—, or—C(Me)₂—, Z₁ to Z₄ each represent a hydrocarbon atom, a hydrocarbongroup, or a heteroatom-containing hydrocarbon group, R′ represents ahydrogen atom, a hydrocarbon group, or a heteroatom-containinghydrocarbon group, and o and p each represent an integer of 1 to
 4. 2.The compound according to claim 1, wherein in General Formula (1), o andp each are
 2. 3. The compound according to claim 1, wherein in GeneralFormula (1), Ar₁ and Ar₂ independently represent a group selected fromthe following formulae,

where, R₁ to R₆ each represent a hydrogen atom, a hydrocarbon group, ora heteroatom-containing hydrocarbon group, and o and p each represent aninteger of 1 to
 4. 4. A resin obtained by polymerization of the compoundrepresented by General Formula (1) according to claim
 1. 5. Apolycarbonate resin derived from the compound represented by GeneralFormula (1) according to claim
 1. 6. An optical molded articlecontaining the resin according to claim
 4. 7. The optical molded articleaccording to claim 6, wherein the optical molded article is an opticallens.
 8. The optical molded article according to claim 6, wherein theoptical molded article is an optical film.
 9. A resin obtained bypolymerization of the compound represented by General Formula (1)according to claim
 3. 10. A polycarbonate resin derived from thecompound represented by General Formula (1) according to claim
 3. 11. Anoptical molded article containing the polycarbonate resin according toclaim
 5. 12. The optical molded article according to claim 7, whereinthe optical molded article is an optical lens.
 13. The optical moldedarticle according to claim 7, wherein the optical molded article is anoptical film.